Chicago
North America · United States
Best Months
Apr, May, Jun, Jul, Aug, Sep, Oct
Rec. Nights
4 nights
Airports
ORD, MDW
Avg. Cash
$52 - $1,801/night
Best Value
Overview
Chicago is one of America greatest cities, sitting on the southwestern shore of Lake Michigan with a skyline that rivals New York. The best time to visit is April through October, when warm weather opens up the city famous lakefront, rooftop bars, and outdoor festivals. Summer brings iconic events like Lollapalooza, the Taste of Chicago, and the Chicago Air and Water Show, while spring and fall offer pleasant temperatures with thinner crowds and better hotel rates.
The city is a paradise for architecture lovers — the Chicago Architecture Center boat tour along the Chicago River is consistently rated one of the best tours in the world. Millennium Park and its iconic Cloud Gate sculpture (The Bean) anchor the downtown experience, while Museum Campus houses the Field Museum, Shedd Aquarium, and Adler Planetarium. Neighborhood hopping is essential: Wicker Park for indie vibes, Lincoln Park for green spaces, and the Magnificent Mile for shopping.
For points travelers, Chicago offers exceptional hotel coverage. With 85 properties across Marriott, Hilton, Hyatt, IHG, and Wyndham, the city is one of the deepest award redemption markets in the country. Properties range from the iconic Palmer House Hilton to the modern Hyatt Centric Chicago Magnificent Mile, with options in every neighborhood and price tier.
Cash vs Points
Hotels in Chicago range from $52 to $1801 per night. Points redemptions offer 11.43+ cents per point value.
Points Hotel Recommendations
12 properties in Chicago bookable with points, sorted by value
| Hotel | Program | Check-in | ||||
|---|---|---|---|---|---|---|
Hyatt Regency O'Hare Chicago | Hyatt | 8,000 | $914 | 11.4¢ | ||
Hyatt Lodge Oak Brook Chicago | Hyatt | 9,500 | $750 | 7.9¢ | ||
Fairmont Chicago, Millennium Park | Accor | 13,892 | $320 | 2.3¢ | May 22 | |
Swissôtel Chicago | Accor | 17,716 | $407 | 2.3¢ | May 22 | |
SpringHill Suites by Marriott Chicago Schaumburg/Woodfield Mall | Marriott | 26,000 | $584 | 2.3¢ | May 22 | |
Sports Illustrated Resorts Chicago | Wyndham | 15,000 | $314 | 2.1¢ | May 22 | |
Super 8 by Wyndham Chicago IL | Wyndham | 15,000 | $279 | 1.9¢ | May 22 | |
TownePlace Suites by Marriott Chicago Schaumburg | Marriott | 30,000 | $551 | 1.8¢ | May 22 | |
Hampton Inn Chicago Downtown/Magnificent Mile | Hilton | 60,000 | $381 | 0.6¢ | May 22 | |
LondonHouse Chicago, Curio Collection by Hilton | Hilton | 75,000 | $473 | 0.6¢ | May 22 | |
Holiday Inn Chicago - Schaumburg | IHG | 32,000 | $198 | 0.6¢ | May 22 | |
Holiday Inn Express & Suites Chicago Schaumburg | IHG | 26,000 | $156 | 0.6¢ | May 24 |
Affiliate Disclosure: Some links on this site are affiliate links. We may earn a commission at no extra cost to you. This helps us keep the site running and continue providing free travel points advice.
Transfer Points Strategy
Find the best transfer path for your credit card points
If you have Points:
Hyatt Regency O'Hare Chicago
If you have ALL Points:
Fairmont Chicago, Millennium Park
If you have Marriott Bonvoy Points:
SpringHill Suites by Marriott Chicago Schaumburg/Woodfield Mall
If you have Points:
Sports Illustrated Resorts Chicago
If you have Hilton Honors Points:
Hampton Inn Chicago Downtown/Magnificent Mile
If you have IHG One Rewards Points:
Holiday Inn Chicago - Schaumburg
Travel Tips
Best Time to Visit
Apr, May, Jun, Jul, Aug, Sep, Oct
Getting There
ORD, MDW
Visa & Entry
Check your country's requirements
Budget
From $52/night
Packing Essentials
Pack for the climate
Cultural Tips
Respect local customs
Ask AI About Chicago
Have questions about traveling to Chicago with points? Our AI advisor can help you plan the perfect trip, compare hotels, and find the best value redemptions.
Ask Travy